Your First 10 Customers Will Be Awkward, Slow, and Underpriced. That's the Job.

A field guide for founders who are tired of being told to "just do things that don't scale." Includes a one-page checklist you can actually use this week.

Photo by dlxmedia.hu / Unsplash

The internet has roughly 4,000 articles about how to get your first 10 customers. I've read most of them. They all say the same five things: build an ICP, use your network, do things that don't scale, talk to early adopters, ask for referrals.

All of that is true. None of it is useful at 7:43am on a Tuesday when you've sent 40 cold emails and gotten one reply, and that reply says "unsubscribe."

So this is a different kind of approach. It's what I actually tell founders when they pay me for an hour of my time and I have 60 minutes to give them something they didn't already read on Y Combinator's blog.

I've worked with 500+ startups over the last decade. The ones who get their first 10 customers all do roughly the same uncomfortable things. The ones who don't get there are usually doing one of three things instead: building, hiding, or LinkedIn-posting.

Let's get into it.

Your first 10 customers are not a marketing problem

Here's the thing nobody on a podcast says out loud: the reason most pre-revenue startups can't get their first 10 customers isn't that their funnel is broken. It's that they have not had 50 honest conversations.

I ask founders all the time, "How many real conversations have you had with potential customers this month?" The answers cluster around three numbers: 3, 7, and "a lot." When I press on "a lot," it's usually 11.

Eleven is not a lot. Eleven is a hobby.

If you're under 10 customers, the math is brutal but liberating: you need to talk to 50 people. Roughly half won't respond. Of the half that do, maybe a third will agree to a call. Of those, maybe a third will become customers. That's how you get to 10. There is no AI tool, no Notion template, no Substack subscription, and no $4,000 cohort-based course that compresses this. Sorry.

Stop hiding behind the product

I once worked with a founder who had spent four months "getting the website right" before launching outbound. The website was beautiful. Award-worthy. He showed me animations.

He had two customers. Both were friends.

The website was a hiding place. So is the pricing page. So is the pitch deck. So is the wait-list. So is the Notion doc titled "Sales Strategy v3 FINAL." So is the LinkedIn post about being "heads down."

You are not heads down. You are hiding. The two things look identical from the outside and feel completely different from the inside, but only you know which one it is. Be honest with yourself, then close the Figma tab.

Charge from day one. Yes, day one.

Every consultant says this. Most founders ignore it. Here's why they shouldn't.

A free customer is not a customer. A free customer is a busy person doing you a small favor. They will not give you real feedback because they are not invested. They will churn the moment something else becomes more interesting. And, this is the part nobody says, they will quietly distort your understanding of what people actually want, because they're not voting with money, only with politeness.

The first time someone pays you, even if it's $50, the conversation changes shape. They start telling you what's actually broken. They start expecting things and they start being a customer.

Charge from the first one. If you're embarrassed by the price, charge that price anyway. Embarrassment is data: it usually means you're closer to the right number than you think.

The awkward follow-up wins the deal

Here's the most unsexy truth in startup sales: the follow-up email gets the deal. Not the first email. Not the demo. The follow-up, usually the third or fourth, is where the close lives. And almost every founder I work with sends one, maybe two, and then gives up because the silence feels like rejection.

It is not rejection. It is a Q4 fire drill. It is a sick kid. It is a layoff that happened the day after your call. It is a CFO who said "let me think about it." It is almost never "I never want to hear from you again."

The founders who get to 10 customers send the follow-up that feels uncomfortable. The ones who don't, don't.

Send the email. Worst case: you find out it's a no, and you can move on. Best case: you close the deal that 99% of your competition gave up on three days too early.

The thing nobody tells you about your first 10

Your first 10 customers will be wrong.

Not all of them, but several. They'll be slightly outside your ICP, paying a price you'll later realize was too low, asking for features you'll later realize don't matter. You will look at them six months later and think, "Why did I sell to that person?"

That's fine, those wrong-fit customers are how you find out what your ICP actually is. The ICP exercise on Day 1 is a guess. The ICP you have after 10 customers is data, the gap between the two is the whole point.

Sell to the wrong people on purpose if you have to. Reject the ICP twice before you trust it.

One more thing: the founders who close

The founders who get past 10 customers tend to share three traits I've noticed across 500+ engagements. They aren't necessarily the loudest, they aren't the ones with the best decks. They aren't the ex-McKinsey ones (sorry).

They are:

The ones who send the awkward email before they've decided if it's a good idea. The ones who don't run away when the prospect goes silent. And the ones who stay specific, about the customer's problem, about their own product, about what they're asking for. Vague founders sell to no one. Specific founders sell to people who didn't even think they needed the thing.

That's it. That's the entire sales consulting industry compressed into three sentences. You're welcome.

The Hands-On Checklist (Print This and Stick It Next to Your Monitor)

Use this every week until you hit your first 10 customers. It's intentionally short. If a checklist takes more than 90 seconds to read, nobody reads it.

🗒️ The First 10 Customers Weekly Checklist

Monday — The Numbers

• How many real conversations did I have last week? (Write the number down. No rounding up.)

• How many follow-ups did I send to people who went silent? (At least 3 = on track.)

• How many new prospects did I add to my list? (Aim for 10.)

  
  

Tuesday & Wednesday — The Outreach

• Sent at least 10 personal, specific emails (not templates) to potential customers.

• Asked at least 1 existing contact for an introduction.

• Resisted opening a new Notion doc to "organize my approach."

  
  

Thursday — The Calls

• Held at least 2 discovery calls.

• In each call, asked the question: "Walk me through the last time you tried to solve this." (This is the best question in sales. Don't replace it.)

• Write down everything what your are listening to in these calls, the information you get will sharpen your whole Go-To-Market Strategy.

  
  

Friday — The Awkward Move

• Sent at least one follow-up to a prospect who has been silent 4+ days.

• Sent a price to at least one warm prospect, even if it scared me.

• Close the laptop before 6pm. Founders who burn out don't close deals.

  
  

End of week — The Honest Question

• Did I do work this week that brings a customer closer, or did I do work that feels like progress but isn't?

• If the answer is the second one, what specifically am I avoiding?

Your first 10 customers don't come from a strategy. They come from 50 conversations, honest pricing, and the follow-up email you didn't want to send. If you're stuck under 10 customers, the question isn't "what's wrong with my funnel", it's "where am I hiding?"

Save the checklist. Or better, print it. The founders who close are the ones who do the slightly embarrassing thing on Tuesday morning.

Want help getting from 0 to 10 — and then to your next $1M? I work 1:1 with founders selling their own product. Book a free 30-minute strategy call →

Or grab the Startup Sales Strategy Workbook → if you'd rather DIY first.